My boss has always been terrible at separating work from personal life. Mostly because her work is her life. She does a lot of happy hours and dinners with our team and is very friendly with everyone.
Today she and I had my 1-on-1 and she asked if I would go to Mexico with her. Fully paid by the company(she owns), but clearly not for work as we don’t have any business there. I was caught so off guard that I didn’t know what to say and said I would think about it.
I don’t think she is into me as she has had an on and off boyfriend for a couple years. She said I’d have my own room and she just wanted to treat me to a trip and thinks we would enjoy the time together. This was all said without any hint of flirting or anything.
I’m not really sure what to think or do about this. She is a great boss and honestly I think its completely innocent. I really like my job and would enjoy a paid trip to be honest. What should I do here?
Comments
Brother. Oh brother.
“She invited me to Mexico with her[….] Without any hint of flirting or anything”
Brotheeeer
I say, if you want to, Go. You’ll get vacation, sex and an experience.
Say yes and go, have fun
Any open positions?
Bro… Even if she isn’t trying to get with you or anything, GO ENJOY THE FREE TRIP!!
Heck yes!!!! Start packing!!!
So next time a friend or family member asks you how you got your new promotion you can say, ‘well I took a trip down to Mexico with my boss for a week and yada yada I got a big promotion’
What happens in Mexico stays in Mexico.
*click. Noice
If this was real …
Never get involved with the boss unless you’re prepared to look for a new job. A drink or two and it can get messy.
You like your job and like your boss (at work).
So you really want to take the chance and F all that up? Think of the countless things that could go wrong on a trip to Mexico. All risk, no reward.
Yolo it and go. Please update us when you get back. Good luck brother!
She probably wants a male companion for safety. She not into you.
Don’t She is your boss. Don’t mix things up.
Don’t dip your pen in company ink. Ever. It’s that simple.
Why is this even being questioned?
Look…. You’re still fairly young and you won’t get this kind of opportunity again at 50 years old. Take it and if things turn out right she will give you bonuses possibly. This is outside of work so it’s not company’s time… but then again she owns the company! Take it and enjoy it
Never shit where you eat. Just sayin’. 😐
“Just got back from Jamaica. Tan almost everywhere, Jan almost everywhere”
Are you Michael Scott from the Office? Is your boss Jan Levinson
Go OP GOOO!!
How are you 32 and this naive, unless this is a shit post.
Hola Mejico
If you are not already committed to another, then strongly consider it, but before you do, think about the repercussions if you do get romantic and that romance eventually ends. What kind of job market exists that you could move into if you have to leave this job.
If you are not getting any sex from her, there are plenty of gorgeous latinas around. Hell yeah I would go!!
Seriously, if you value your integrity, you would say no. I don’t really know what her true intention may be, but going on a holiday with a boss, it gives people certain impressions.
It’s totally up to you. But remember, no one knows what happened. And no one thinks nothing happened.
If you go, you’ll know that you have the same trouble as Boss does.
I’d go and play it by ear. Could be a lovely vacation with a friend. Could be a sex filled vacation with a new lover. Could blow up. If the communication is there it can be navigated. Just remember you can’t really ghost her.
I’m surprised nobody has mentioned the most obvious thing to you. She is inviting you to legitimize this as a “work” trip in front of the IRS. If the IRS audits her, you will be a witness. Think about that carefully.
I would go. Enjoy your trip
Don’t ever mixed personal and work life, if I were you I’d decline unless, you also like her and is prepared to look for different job later on when things get serious
Hmmm…
>WorkingAtTheOffice
>0 d
Reddit Age
Why wait until vacation. Start sex tonight! What could go wrong? Everything! A real lose lose situation.
Tan almost everywhere, Jan almost everywhere, hee hee
Ask around and see if she has given this type of thing as a bonus to any other employees.
Just take what comes with a chuckle and the worst you can do is some bad sex and a free vacation. Maybe the sex will be spectacular. Who cares? Be safe and have fun.
Looks like she want to be your sugar mama
Has she every taken anyone else on holiday before? Will it be a thing that everyone is aware of and will also have a chance in the future? If so go for it, maybe she just wants someone to hang out with.
So a scenario would be if she knocks on your door and you turn her down. How would that play out for your actual work, you know, where you get paychecks to support yourself and pay your rent?
What do you think she gets from paying for your vacation?
I want the update on this.
So I would probably go but just remember this, it may cost you your job lol.
Mixing business and pleasure is always a risky proposition. If things go great you might get a promotion and own the company at some point ha ha
If things go badly then you might end up looking for a job at the end of the vacation.
That being said I’d say go for it what the heck!
If you don’t care about the job and welcome the free sex, then yes. Otherwise, say no.
Please remember: nothing in this life is free. So if this goes horribly wrong, don’t come back here complaining and asking what to do.
Go
You need to say yes, other wise you will unemployed soon 😉 .
Wylie probably should go just have fun man.
Just go.
This is a shit post
Yes, but if you have reservations about this being non-platonic, ask her how she’d feel if you invited your partner to come too (who would pay their own way). Read the reaction.
Ugh. My only question would be how do I get out of this gracefully. Maybe your grandma is dying and you cant take the chance of being far away at such a tenuous time?
💯 No. This could be a set up – don’t know what sort of setup but this sounds fishy as f
Ummm, we will need her picture posted here to give you a full and accurate assessment of this situation. Otherwise, perform well and come home a (richer) man.
Do it and enjoy it.
Whatever happens will happen and when you are an old man, you’ll look back and remember you used to be adventurous. It’s just life, don’t take it so seriously
The trip off IS the flirting, genius.
Didn’t see anyone else asking, but do you have a girlfriend or a wife?
If so, you should not go. If not, you should go. Simple as that.
Also, if she wants to fuck, and you’re into it: just do it and enjoy yourself man. Life is too short to get caught up in feelings when you don’t have to.
Sometimes sex is just sex. Ain’t gotta be nothin more than that.
Oh I’m definitely going to
This is not innocent you dumbo. If you have any sense of values and morals you will turn her down and find new employment.
If she was taking an entire team of say 10 people to Mexico, that would be fine. This isn’t not that. This is a booty call trip.
YOLO
Nice, Nice!
No, don’t go. It’s not going to work out in the end and she may get fired.
Man GO 🤣🤣
We need pictures of her
Unless you have a significant other, go for it. I’ve been on business trips to resort type places just me and a female colleague and it was an awesome, platonic time.
Yeah, I get women asking me to go to Mexico all the time, all platonic and everything. 🤦♂️
Sounds like you’re the only that doesn’t think sex is on the table. But hey, if you get along that well with her that you can just enjoy each others company go have fun.
Not clear from your note whether you will be using your vacation time in joining her or she intends to treat it as your work time. If the former, then certainly she has other intentions.
Assuming you won’t be too devastated if you lose that job, I’d go ahead and play it by ear.
I am a woman and I had a direct report who was a dude and also a very good friend. We were both from NYC and we both moved to SF a few years apart. I was his manager in both cities.
We spent nearly every weekend together exploring California. When my mom purchased a house in Palm Springs, he came with me to hang out for a weekend.
There were absolutely zero romantic feelings. We just really got along and liked to do the same stuff.
Go
You have obligations like a birthday party or wedding during the planned time away. But you are grateful for the consideration. Separate rooms? What else would you expect her to say straight off the bat? You could always then be invited to her room for pre dinner drinks at your peril.
The optics are so bad, my friend. Extricate yourself with politeness and self respect.
Everyone saying have sex with your boss is crazy. That could get ALL kinds of crazy and you may end up losing your job.
Oh it’s that.
If she hasn’t given you any reason not to trust her, then trust her. It sounds like she really just wants to do something nice for you. Go for it. If not, lmk and I’ll come work for her and take a free Mexico trip!
Nah, don’t do it! Too akward!
Ole’
If you don’t go on this trip your a fool haha relationship building or not its a free trip and new experience. Shit I wish I was invited on a trip
I personally miss so much with flirting. My wife tells me, you know she was flirting with you. What. I never saw it. I am not autistic and have lots of empathy. I miss seeing flirting, maybe because it doesn’t interest me. If you also are like me, you might be missing the hints and tips that are being sent. If you are single and up for a bit on the side, then go for it and see what happens, if you are in a relationship or find a bit on the side distasteful, you might just cruel a friendship. Your decision anyway. We don’t know your thoughts or those of your boss.
Once out of sight and earshot of the office, anything could happen. You don’t KNOW what she wants, only what she says she wants. If you go, you are sort of in her control and on her turf. You might be expected to go to pound town with her. OTOH you might be expected to behave yourself. You need to be able to synchronize with her and if you reject her advances, or assume too much and make advances of your own, it will negatively affect your job. If you hook up, then it’s on her terms and you are not the alpha in the relationship.
Her desire for a male companion might be totally innocent. She might just want you along to help her fend off unwanted advances, especially if she is kinda hot and gets irritated by every swinging weiner twitching her way and every would-be Romeo bombarding her with stupid pickup lines. But the dirty old man within me says she wants to jump your bones. That guy has almost got me killed a couple of times but sometimes he hits the mark true and square.
If you like your job just the way it is, don’t go. If you are okay with throwing the dice, then go, put your bet out there, and see what it gets you. You can always get another job. Actually you can always get another GF or another one night stand, too, for that matter. But I promise you, if you go, things probably will change. Maybe for better, maybe for worse.
If you decide to go, be ready with your response in case she does hit on you. If you reject her advances, there may be fallout.
Are you married or have a SO? If so then the answer is no. If not then I would go and enjoy the time, get to know her better and see how innocent it is. You can always say no to anything sexual and record those conversations to protect yourself. You might become really good friends and get a free vacation.
“Thank you so much for the invitation, but I won’t be able to make it.”
if the roles were reversed, the ppl on this sub would prollyyyyy be singing a completely diff tune hahahahaha butttt nobody likes a sourpuss so…. GO DUDE!
Give her what she wants and then ask for a raise when you get home…
Don’t do it, this could blow up in your face!
Go. But make sure you eat that thang and pound it right
I think this is innocent. Just go on the trip and enjoy yourself, try to come up with some fun friendly surprise for her as well to return the favor.
There are a lot of nice people without agendas in this world.
When you’re off work with people in your company you really are not off work! I would say this is particularly true if the person wanting you to go is the owner of the company you work for.
Expect to lose your job if your dick fails you.
Bangboss instead of bangbus
Is it like that or not? Just fucking go and find out. It sounds like she’ll be able to handle it regardless. It’s another story if you can’t
Make sure you treat her kindly, open the door for her, grab her a towel, rub on the tan lotion and by the end of the trip you both will be exhausted.
An HR nightmare waiting to happen. You go on business trips with your boss. You don’t go on vacation with them.
Wierd. Keep it strictly business & don’t accept.
I’d go if I was single for sure, I could really use a free vacation lol. But if I was in a relationship I couldn’t go and disrespect my partner.
NO. Just NO.
She is not a friend. She is your boss. She will always be your boss. Keep her at arms length unless you can get another job immediately. Things could go south real quick. She could make a pass at you and then what are you going to do? Have sex with her? Then what? You are still her employee. If she pays then you OWE her. Maybe not with sex but hey OP I need you to work late because I PAID for your “vacation “. Or Sorry OP no RAISE for you because I paid for your “vacation”.
Again NO.
If you’re single, go to Mexico!
Enjoy a free vacation, and hopefully, your bosses body every night
Go and get her pregnant. Then it will be your company to.
If you perform well on this vacation, there may be a lot more out of town travel with your boss in future.
I’ll go if you don’t
Go. Don’t think. Just go.
She wants to fuck you. Take it, I’d say.
Go bang the shit outta her bro
Go enjoy just don’t pressure for sex, but if she wants it, make sure an overperformed
Maybe she doesn’t wanna travel alone. Go. Have fun. Don’t fuc* !
Are you attracted to her? That’s a real question you have to ask yourself. Then you need to ask if you’d be willing to risk your career over that attraction. Answer those two things and you’ll have your answer.
This was my favorite episode of The Office…
I find this interesting and wonder how would it play out if the genders were swapped. Would there be a lot of female redditors calling the boss a creep and get HR involved? 🤔🤔
Go man. Maybe she jumps your bones, maybe she doesn’t. Either way, free trip.
I would but I’m also known to make terrible decisions.
Don’t go to a Coldplay concert
She’s 38. At this age, they know exactly what they want.. She’s tryna fuhhhhhq
If I was single. YOLO.
You may think it’s innocent.
She may say it’s innocent.
How do you explain this to other management and coworkers? How would you explain to your fellow coworkers why you were invited and they weren’t? What makes you so special?
Oh, the water fountain gossip will be so juicy. Would love to be a fly on the wall.
No one will look at you or work with you the same ever again. Might want to brush up that resume. And practice how you’ll explain this favoritism to potential employers AND anyone from the company you’d want as a reference (if you could trust anyone to give a glowing reference after this 1:1 getaway to Mexico).
updateme
“Tan everywhere. Jan everywhere. So Jan and I went to Jamaica”.
-Michael Scott
If you dont go and dont update us….
Do you want to go to Mexico? It’s just a job. Life is supposed to be fun
Bring your GF
I have a friend who hates to traveling alone, she gets lonely, her families all dead, and her ex is a asswipe
Go on the free vacation and have a great time. Just be prepared to lay down the pipe because she absolutely is DTF.
These things have never happened to me. Also never had a hot step-mom. Why has fate been so cruel to me
Deciding factor: is she hot?
Sounds like she sold one of your kidneys!
You’re kind of hooped either way now.
If you value your reputation in the industry, tell her no.
If you really like your job and would enjoy a paid trip, you should NOT go on a vacation with your boss and you should pay for your own trip to go anywhere you like.
DON’T MESS AROUND WITH YOUR BOSS WHO OWNS THE COMPANY YOU WORK FOR or you won’t be working there much longer.
I volunteer as tribute. I will take this trip in your place. No need to thank me. I know getting a free trip is a burden and a free room and free food and free drinks is just awful. I sympathize with you.